Evaluation of the anti-inflammatory activity of some pyrrolo[ 2,3 - d ]pyrimidine derivatives
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Med Chem Res (2013) 22:2244–2252 DOI 10.1007/s00044-012-0217-5
ORIGINAL RESEARCH
Evaluation of the anti-inflammatory activity of some pyrrolo[2,3-d]pyrimidine derivatives Mosaad S. Mohamed • Rehab Kamel Rania H. Abd El-hameed
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Received: 1 March 2012 / Accepted: 24 August 2012 / Published online: 6 September 2012 Ó Springer Science+Business Media, LLC 2012
Abstract A series of novel pyrrolo[2,3-d]pyrimidine and fused pyrrolo[2,3-d]pyrimidine derivatives were synthesized and their structures were characterized by elemental analysis, 1 H NMR, IR, and mass spectroscopy. Their in vivo antiinflammatory activities were evaluated, and the results indicated that some of the title compounds compounds showed significant activities. These compounds are 2b ((7-(4Methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-hydrazine), 7b (4-(2-(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine), 7d (4-(2(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine), and 9b (4-(3,5-Dimethyl-4H-pyrazol -1-yl)-7-(4-Methoxyphenyl)-5,6-diphenyl-4,7dihydro-3H-pyrrolo[2,3-d]pyrimidine). Keywords Pyrrolo[2,3-d]pyrimidine Pyrrolo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine Anti-inflammatory activity Structure–activity relationship
Introduction Inflammation is a normal protective response to tissue injury caused by several causes (Mycek et al., 1987). Inflammation is triggered by the release of chemical
mediators from the injured tissue and migrating cells where prostaglandins play a very important role as mediators in the process of inflammation. Almost all classes of nonsteroidal ant-inflammatory drugs (NSAIDs) inhibit the conversion of arachidonic acid to prostaglandins. The carrageenin-induced rat hind paw edema test is a common model for evaluation of anti-inflammatory agents; in this model, cyclooxygenase-2 (COX-2) levels are raised and this is accompanied with the increase in prostaglandin production (Huslisson, 1983; Evans and Nigel, 1987). Pyrrolo[2,3-d]pyrimidine derivatives have attracted a great deal of interest owing to their medicinal activities as they have wide variety of interesting biological activities such as anti-microbial (Rao, 1968; Dang and Gomez-Galeno, 2002), analgesic (Danchev et al., 2006), anti-inflammatory (Jarvis et al., 2002), antiviral (Gangjee et al., 2005), and anti-cancer (Declercq et al., 1987; Krawczyk et al., 1995; Finch et al., 1997). The rapid growth in the literature dealing with the synthesis and anti-inflammatory activity of the pyrrolo[2,3-d]pyrimidine derivatives prompted us to synthesize new derivatives of pyrrolo[2,3-d]pyrimidine and fused pyrrolopyrimidine derivatives and test their antiinflammatory activity as an extension to our previous work (Mohamed et al., 2012).
Chemistry M. S. Mohamed R. H. Abd El-hameed (&) Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Helwan University, Ein Helwan, Cairo, Egypt e-mail: [email protected] R. Kamel Toxicology and Pharmacology Department, Faculty of Pharmacy, Helwan Universi
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